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cryptography: PKCS#7 EnvelopedData decryption exposes a Bleichenbacher oracle through distinguishable errors and timing

High severity GitHub Reviewed Published Jul 31, 2026 in pyca/cryptography • Updated Aug 3, 2026

Package

pip cryptography (pip)

Affected versions

>= 44.0.0, < 50.0.0

Patched versions

50.0.0

Description

Summary

pkcs7_decrypt_der, pkcs7_decrypt_pem, and pkcs7_decrypt_smime reported the
outcome of decrypting a RecipientInfo's encryptedKey in several
distinguishable ways, one of which disclosed the exact length recovered from the
RSA operation. The same distinction was also observable by timing. An
application that decrypts attacker-supplied EnvelopedData and reflects the
outcome gives the attacker a Bleichenbacher oracle against the
content-encryption key.

Introduced in 44.0.0. Fixed in 50.0.0.

Details

Decryption ran as: RSA PKCS#1 v1.5 decrypt of encryptedKey → build an AES
cipher from the result → AES-CBC decrypt and PKCS#7 unpad. Each stage failed
differently, with no RFC 3218 mitigation:

  1. invalid RSA padding → Decryption failed
  2. valid padding, bad key length → Invalid key size (N) for AES., disclosing N
  3. correct length, wrong key → Invalid padding bytes.
  4. the real key → plaintext

Case 1 is reachable only where the linked library lacks implicit rejection:
OpenSSL 3.0 and 3.1, LibreSSL, and BoringSSL. On OpenSSL 3.2+, used in our wheels,
invalid padding instead returns a synthetic plaintext of
pseudorandom length, so the error channel does not distinguish conforming
ciphertexts.

Exploitation requires a service that auto-decrypts untrusted EnvelopedData
matching the victim certificate and answers adaptively at high volume, such as
an S/MIME gateway or mail filter.

Fix

Per RFC 3218, the content-encryption algorithm is now resolved before the
private key is used, so the expected key length is known in advance. If the RSA
decryption fails or recovers a key of the wrong length, a random key of the
expected length is substituted and decryption continues down an identical path.
All failures now report identically and perform the same work.

Not addressed by this fix

EnvelopedData does not authenticate its content. Tampering with
encryptedContent alone yields a CBC padding oracle that recovers plaintext at
roughly 256 queries per byte, without recovering any key, on every backend. This
is a property of PKCS#7 rather than of this implementation, cannot be fixed in
the library, and is now documented.

Credit

Reported by @X1AOxiang.

References

@alex alex published to pyca/cryptography Jul 31, 2026
Published to the GitHub Advisory Database Aug 3, 2026
Reviewed Aug 3, 2026
Last updated Aug 3, 2026

Severity

High

CVSS overall score

This score calculates overall vulnerability severity from 0 to 10 and is based on the Common Vulnerability Scoring System (CVSS).
/ 10

CVSS v4 base metrics

Exploitability Metrics
Attack Vector Network
Attack Complexity High
Attack Requirements Present
Privileges Required None
User interaction None
Vulnerable System Impact Metrics
Confidentiality High
Integrity None
Availability None
Subsequent System Impact Metrics
Confidentiality None
Integrity None
Availability None

CVSS v4 base metrics

Exploitability Metrics
Attack Vector: This metric reflects the context by which vulnerability exploitation is possible. This metric value (and consequently the resulting severity) will be larger the more remote (logically, and physically) an attacker can be in order to exploit the vulnerable system. The assumption is that the number of potential attackers for a vulnerability that could be exploited from across a network is larger than the number of potential attackers that could exploit a vulnerability requiring physical access to a device, and therefore warrants a greater severity.
Attack Complexity: This metric captures measurable actions that must be taken by the attacker to actively evade or circumvent existing built-in security-enhancing conditions in order to obtain a working exploit. These are conditions whose primary purpose is to increase security and/or increase exploit engineering complexity. A vulnerability exploitable without a target-specific variable has a lower complexity than a vulnerability that would require non-trivial customization. This metric is meant to capture security mechanisms utilized by the vulnerable system.
Attack Requirements: This metric captures the prerequisite deployment and execution conditions or variables of the vulnerable system that enable the attack. These differ from security-enhancing techniques/technologies (ref Attack Complexity) as the primary purpose of these conditions is not to explicitly mitigate attacks, but rather, emerge naturally as a consequence of the deployment and execution of the vulnerable system.
Privileges Required: This metric describes the level of privileges an attacker must possess prior to successfully exploiting the vulnerability. The method by which the attacker obtains privileged credentials prior to the attack (e.g., free trial accounts), is outside the scope of this metric. Generally, self-service provisioned accounts do not constitute a privilege requirement if the attacker can grant themselves privileges as part of the attack.
User interaction: This metric captures the requirement for a human user, other than the attacker, to participate in the successful compromise of the vulnerable system. This metric determines whether the vulnerability can be exploited solely at the will of the attacker, or whether a separate user (or user-initiated process) must participate in some manner.
Vulnerable System Impact Metrics
Confidentiality: This metric measures the impact to the confidentiality of the information managed by the VULNERABLE SYSTEM due to a successfully exploited vulnerability. Confidentiality refers to limiting information access and disclosure to only authorized users, as well as preventing access by, or disclosure to, unauthorized ones.
Integrity: This metric measures the impact to integrity of a successfully exploited vulnerability. Integrity refers to the trustworthiness and veracity of information. Integrity of the VULNERABLE SYSTEM is impacted when an attacker makes unauthorized modification of system data. Integrity is also impacted when a system user can repudiate critical actions taken in the context of the system (e.g. due to insufficient logging).
Availability: This metric measures the impact to the availability of the VULNERABLE SYSTEM resulting from a successfully exploited vulnerability. While the Confidentiality and Integrity impact metrics apply to the loss of confidentiality or integrity of data (e.g., information, files) used by the system, this metric refers to the loss of availability of the impacted system itself, such as a networked service (e.g., web, database, email). Since availability refers to the accessibility of information resources, attacks that consume network bandwidth, processor cycles, or disk space all impact the availability of a system.
Subsequent System Impact Metrics
Confidentiality: This metric measures the impact to the confidentiality of the information managed by the SUBSEQUENT SYSTEM due to a successfully exploited vulnerability. Confidentiality refers to limiting information access and disclosure to only authorized users, as well as preventing access by, or disclosure to, unauthorized ones.
Integrity: This metric measures the impact to integrity of a successfully exploited vulnerability. Integrity refers to the trustworthiness and veracity of information. Integrity of the SUBSEQUENT SYSTEM is impacted when an attacker makes unauthorized modification of system data. Integrity is also impacted when a system user can repudiate critical actions taken in the context of the system (e.g. due to insufficient logging).
Availability: This metric measures the impact to the availability of the SUBSEQUENT SYSTEM resulting from a successfully exploited vulnerability. While the Confidentiality and Integrity impact metrics apply to the loss of confidentiality or integrity of data (e.g., information, files) used by the system, this metric refers to the loss of availability of the impacted system itself, such as a networked service (e.g., web, database, email). Since availability refers to the accessibility of information resources, attacks that consume network bandwidth, processor cycles, or disk space all impact the availability of a system.
CVSS:4.0/AV:N/AC:H/AT:P/PR:N/UI:N/VC:H/VI:N/VA:N/SC:N/SI:N/SA:N

EPSS score

Exploit Prediction Scoring System (EPSS)

This score estimates the probability of this vulnerability being exploited within the next 30 days. Data provided by FIRST.
(7th percentile)

Weaknesses

Observable Timing Discrepancy

Two separate operations in a product require different amounts of time to complete, in a way that is observable to an actor and reveals security-relevant information about the state of the product, such as whether a particular operation was successful or not. Learn more on MITRE.

Generation of Error Message Containing Sensitive Information

The product generates an error message that includes sensitive information about its environment, users, or associated data. Learn more on MITRE.

CVE ID

CVE-2026-69247

GHSA ID

GHSA-g6cj-pr64-35w5

Source code

Credits

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